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Crossdressing

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9

The Next Night - Crossdresser: Part 2 of 2

The next night and a second session with Jenny.

I woke up early from the sunlight shining through the windows. We’d forgotten to close the curtains when we collapsed into bed last night. Jenny was already awake and watching me.  ‘I was just about to wake you up with a blow job,’ she smiled. ‘Funny, I was thinking of doing the same to you!’ I laughed. Jenny kissed me then turned around in the bed to lay on her side so our cocks were...Read On

10

The Adventures of Kristof and Marci Part 2

Marci continues Krissy's slut training, putting her maid into some uncomfortable situations...

ADVENTURES OF KRISTOF AND MARCI PART 2 Training     As I stood outside the study, my mind was racing, the day had been pretty exciting already and it was only mid afternoon; what else was to come I wondered with excitement.   After a few minutes, Marci came down and entered the study and I followed.   ‘I told you to wait outside; you come in when I...Read On

6

My Good Friend Pete

A background into our relationship with Pete.

My history with Pete goes back twenty five years, and for most of that time, he has known of my penchant for crossdressing. He also knew that I'd worn most of his wife's wardrobe, and of my preference for the contents of their laundry basket over Annabelle's underwear drawer.  Pete played the leading man role in many of my wife's fantasies. Tall, dark, and ruggedly handsome, who could...Read On

3

Dawn Summer

Oppressed and Underage. Sometimes you just got to take matters into your own hands.

As I climbed aboard the bus, I couldn’t help but feel a sense of relief at my escape. I never realized how free I could feel finally escaping my father for good. Maybe, I should back up a little bit for those of you just catching up to my story. My name is Dawn Summer. I grew up a rich little boy with a father who never quite understood, or cared to understand me. I wanted to become an...Read On

5

Jenny & Mike: Fantasy Sunday

A day of fantasy role-playing with more crossdressing and strapon action.

MICHELLE’S POV The alarm was buzzing, and I couldn’t understand why. We never set it to go off on Sundays. I tried to open my eyes as best as I could. It was only 9 a.m.! I reached over and tried to shut the darn thing off. After a couple of failed attempts, I finally found my target. The awful noise stopped. I turned around realized that James was no longer in the bed with me. “James?” ...Read On

9

Weekend Discovery 1

Friday had finally arrived. Andrew Lippincott glanced at the Rolex on his wrist and then began to pack his attaché case. It was only 4:00 pm but he was the office manager and one of the perks that came with this title was the ability to leave early. Winter had the city in its grasp and a travelers advisory had been posted.That meant there would be no unannounced guests to prevent him...Read On

19

My oddesy 2 - Liam

A friend cheers me up

It had been a few weeks since Glen's puzzling rejection and I was in a slump. I hated my body more than I had in years. Not even sneaking into my sister's old room and playing dress-up could cheer me. And my best friend noticed. Liam was in most of my classes at school and we knew each other since third grade. He had olive skin and a solid German build. Noticing my gloomy disposition he...Read On

16

Made Maryanne

John is unaware of the female power to crush his manhood

It was 3 am. I was busy whacking myself off in the bathroom when Beatrice caught me. She and I had only been together for a few weeks when I started taking a special interest in her underwear. I loved the smell of her wet pussy, combined with the cozy softness of the cotton panty gusset pressed against my nose. Wearing one pair, feeling the delicate material clinging tightly to my ass, I held...Read On

16

The Frederick's of Hollywood Lingerie Model

Courtney's first job in Hollywood is as a Frederick's lingerie model.

When I first arrived in Los Angeles, I was staying at a motel on Sunset Strip in Hollywood. I had plans on working as a tranny call boy there. In the "L.A. Express" magazine, I saw an ad for a club on Sunset, called the Leather and Lace Lounge, that was popular with trannies and the men who liked them. I decided to go there and learn more about the tranny scene in Hollywood. It was three in...Read On

10

How Andrew became Andrea - The Conclusion.

It was easily one of the best summers of his teenage years. Now along with being allowed to indulge himself in his secret desire, he had sex with the stunning Lacy on a regular basis. She had become a friend, lover, employer and tutor. When school resumed in the fall he was forced to limit his visits as there was homework and studies that needed his attention. However when his parents went...Read On

4

Leigh and Leila - Fantasy of a First Night

CD Leila gets read for her first encounter with her girlfriend.

“I don’t know when to stop talking, do I?” I asked. You smiled and kissed me again. It took my breath away. I closed my eyes and let myself get lost in the feeling. It was like nothing I’d ever imagined, nothing I’d ever felt before, nothing I could imagine living without. Your fingers moved just the slightest bit. I nearly came, my cock straining hard against the white satin thong. Your...Read On

10

In Her Shoes Part 3

This is the final part so please read both other parts to this story to understand it fully.

I guided Peter into the main shopping mall in town leading him straight into a shoe shop. The girl in the shop fetched a few pairs for me to try on and I relished asking Peters opinion. He tried not to look too obvious that he was hooked on my shoes and feet. I 'hummed' and 'ahmmed' a short while, telling the girl I was undecided and may well be back later. Grabbing his arm once more we...Read On

An Unexpected Love Story

What was supposed to be a night of dressing turned into a night of making love.

I was so looking forward to Friday. My latest order of lingerie was scheduled to be delivered and knew that I would have some time after closing to try it all on. I own a small business and I work alone on Fridays for this very reason, it gives me time to indulge my secret passion. Getting dressed really helps me relax after a stressful week and have a back room where I can also take pictures....Read On

15

Falling for Zak

A young man let's himself go to another man's desires

I hadn’t noticed the time, and I’d missed the last train home. The student party was fun, but I was in a bit of a panic not knowing what to do. People were leaving, and the crowd was thinning out. If it had gone on for several more hours, I would have stayed there and taken the first train in the morning, but that didn’t look likely. The hostess was already clearing up. I figured she’d...Read On

2

A Break in Action

Settling into a new life is easier than first imagined.

I took a good long look at my now shoulder length hair. It still looked very straight and masculine in contrast to my wig, but at least I had something to work with now. I decided that it was about time to start wearing my natural hair instead of the very nice, but still uncomfortable wig I’d used for four months now. Since I’d left my old life, my chest had grown between an A and B cup...Read On

28

The Meeting

Some first meetings turn out better than others

I initially met Richard through a TG Community site and we seemed to hit it off from the very start.   He was very open about his likes and dislikes, about him being a TG admirer, about having had a fair number of encounters and dates, but he never pressured to know anything about me.   Drawn by his gentleness and gentleman ways though I found myself sharing my deepest dreams and...Read On

9

My First Time Final Chapter

The conclusion of this story

The Friday that Lydia told me about had finally arrived and she would be bringing some of her friends over for drinks after work, and I was to serve them as Melissa. Lydia had also advised me that unlike the dominatrix persona I used during my first outing on Halloween, Melissa the maid, was totally subservient. That morning after my usual visit to the gym I cleaned the house and set up...Read On

13

A Night of Firsts pt 1

So many firsts for a shy gurl while traveling

'Oh my God, this was the night,' I thought to myself. 'I'm finally going to go out dressed.' I work for a small company and get to travel a bit, but I've really only dressed in hotels when I could drive as flying with all my things makes me really nervous. The idea of me and a travel bag being examined and having a stranger discover my femme things just didn't do it for me. However, this...Read On

12

Jaime's Way (part 2)

Sherry has transformed Jaime into a sexy slut

I awoke to feel the dried cum on my face, ass and balls, and then remembering how I got that way made me smile. Crawling out of bed I made my way to the bathroom and took a hot shower and then easily shaved my already smooth legs. Out of the shower I brushed my hair and did what I could to make it appear more feminine. After I put on my make up I walked back to the bedroom and slipped into a...Read On

25

Taking That First Step

A story from the seventies

Lance was seated on a bench on the tree-lined sidewalk waiting for the store to open. Despite the warm morning air he began to sweat and his heart pounded in his chest, this was a bold step for him. Now, this particular store was located in an older but still very popular outdoor shopping center despite the malls springing up everywhere. It was commonly referred to as a specialty shop,...Read On

22

My Sexual Odyssey Part 2: Becoming a Slut

A continuation of the journey described in part 1

After having had a few experiences, I became slightly more comfortable with my sexuality. I decided to branch out a bit, and see what life had to offer. I wondered whether there were any bars or clubs that I could go to to meet people who were looking for someone like me, so I went online and discovered, that yes, there were quite a few such places. It is so wonderful having the internet...Read On

24

Becoming Chloe - Part 6

Friday night - part two: A dream comes true.

My hands trembled as I slipped on my new stockings, and it took me all my concentration to attach them to the suspenders that hung from my waspie. Of course, all this was made the more difficult because of the stunning new 38B's I'd just acquired, and I had to stop myself from keeping my hands off them, plus, they were slightly in the way as I bent down to attach the stockings. Calm down,...Read On

8

Master's Reminder

I had been seeing Master John for about a year now and thing’s were going well or so I thought!

I had been seeing Master John for about a year now and thing’s were going well, or so I thought. I arrived at his home like any other weekend in the outfit he wanted me to wear for my punishment. He would always choose the week before and I knew that there was no argument whatever he wanted he got. I hoped that I had got everything just right for him. Anything slightly out of place or...Read On

17

The Long Walk

The longest walk to my mailbox, ever.

Friday . I get home from work around 9:30, and I head straight for the shower. Now most stories like this involve shaving smooth and things like that, but I'm not able to shave because my wife doesn't care for it. After my shower I go into my closet and get my clothing. I get my black bra and thong and slip into those, followed by tan hose and regular clothes. I have the rental company pick...Read On

17

A Friend With Something Extra.Part 3

Grant collapsed on carpeted floor of the living room. The ropes of semen his friend shot on his chest were beginning to crawl down to his bra. The ones on his bra were slowly moving down toward his belly. His tiny silky bikini panties were filled with his own cum as the sight of his friend's cock shooting on him had gotten him off. He looked up at Ian who was still sitting on the couch with...Read On

7

Mistress Lucy takes control

Power reversal; the usually sissy crossdresser Lucy has fun with her girlfriend, Belle.

Belle had finished disrobing and stood in her bra and thong, both pink, following Lucy's command. The latter stood in front of her girlfriend and, with a light touch of the shoulder, pushed Belle down on to the bed. Belle looked up at Lucy expectantly, eyes wide. Neither girl wore any makeup; they'd been awake for a couple of hours and, having spent the morning in the kitchen loafing around...Read On

13

Exploration (Discovery II)

Shauna's second lover.

After my neighbor, Jack, caught me dressed and made me his girl, my mind was awash with conflicting thoughts and emotions. I had been dressing as an added thrill to masturbating for years, and had fantasized about being with a man, but always considered it just fantasy. I never thought of actually doing it, but now, it had gone from fantasy to reality in just a few hours. Not only had I...Read On

6

Confessions of a Sex Crazy Cross Dresser Part 8

Sandy's adventures continue in Chapters 15 and 16 of book #1

Chapter 15: Dangerous Duo I woke up the following morning to an empty bed. I went to the bathroom and when I came out there was a knock on the door. I looked out and saw Peggy with a bag and two cups in her hands. Upon opening the door, Peggy came inside and placed the drinks and bag on the table and gave me a kiss. “I thought you might want some breakfast,” she said. She had on a...Read On

16

Jenny and Mike: Date Night

A loving husband and wife begin a long weekend of crossdressing and pegging.

It’s Friday night, but for me and my wife it’s Date Night. Most couples have date nights on Saturday, but we have it on Friday nights to get an early start on the weekends. Michelle and I have been married for a little over two years now and we live a very happy life. I was not always so happy because I am a crossdresser and have been dressing up ever since I was 16. I met Michelle when we...Read On

11

Telling Mom I'm A Crossdresser part 13.5: Missy Brings Home A Stud

the continuation to Missy going out and finding a man.

I told Thomas all the details of why I was out this night and he loved the idea. He took one of his Viagra and he led me out of the bar. I felt a little embarrassed at all the cum leaking down but some of the cross dressers were just smiling at me like they were saying “you go gurl!” which made me a little proud. Thomas followed me in his car until we got to my place and I took him by the...Read On